West-of-Trail VIBE:

Hottest Mainland Area
Prestigious & Historic
Small Town City Living

About West-of-Trail

Just minutes to the spectacular beaches of Siesta Key and Downtown Sarasota and tucked along the sparkling waters of Sarasota Bay is the prestigious and historic West-of-Trail district. West-of-Trail, West of 41/South of Mound/North of The Landings, is comprised of numerous charming neighborhoods made up of Spanish style Casitas, Florida Bungalows, newer Custom Builds along with beautifully Updated Homes, and opulent Waterfront Estates. Historic and exemplary Southside Elementary School is an award winning grade-A school and anchors this mostly “local-full time” resident neighborhood. An amenity rich village flanked by South Royal Palms is the epitome of small town living. With restaurants, boutiques, bars and the flagship Morton’s Gourmet Market – featuring a world class wine selection and every delicacy you could wish for. West of Trail is home to Sarasota Memorial Hospital – one of the largest public health systems in Florida and one of Sarasota County’s largest employers with about 5,000 on staff, 800 physicians and 1,000 volunteers, many of whom proudly reside West of Trail/West West of Trail! The historic charm is still evident along the numerous canopied streets and the location, with its proximity to downtown Sarasota and the Bayfront, is what keeps West-Of-Trail one of the hottest residential areas of Sarasota.

Cherokee Park

Established in the 1920’s and one of Sarasota’s oldest and most beautiful neighborhoods, bayside Cherokee Park is highly coveted due to its charm and proximity to the beaches, shopping, hospital and dining as well as all of the culture and liveliness that downtown Sarasota has to offer. Spanish style, Traditional and Florida bungalows, newly remodeled homes and new construction luxury estates mingle among lushly landscaped yards and hug the Bayfront along Sarasota Bay.

Oyster Bay

Quiet canopied streets, lush landscapes and the glistening waters of Sarasota Bay make up this prestigious neighborhood West-of-Trail. One of Sarasota’s most esteemed and private yacht and boating clubs, The Field Club, anchors Oyster Bay and the surrounding executive residences, Florida Ranchers, classic Old-Florida Homes and Waterfront Estates. The ample lot sizes in this neighborhood are ideal for families or those seeking a bit more privacy and room to sprawl.

Harbor Acres

Just south of downtown, nestled along Sarasota Bay, sits one of Sarasota’s most sought-after enclaves, Harbor Acres. Meticulously landscaped streets boast elegant Waterfront Estates and opulent Spanish-style Gated Mansions all with stunning views from every angle. One of the best-located neighborhoods, Harbor Acres has excellent deep water boating and is within walking distance of Selby Gardens, Downtown Sarasota, Sarasota Memorial Hospital and all of the shopping & restaurants of Hillview and Southside Village.


Avondale’s history began in the housing boom of the 1920’s. The neighborhood was originally developed by the Sarasota Improvement Company for families of average means, Seventy-five lots were advertised at $250 each with a down payment of $50 and $10 per month. A number of the lots were sold in 1923 to Irving Bacheller, Edward Brewer and Fred Woolley who then formed a company, the Bacheller-Brewer Corporation. The men subdivided and enlarged the lots, widened the streets, installed a water system and built a sea wall along the Hudson Bayou and dredged the bayou for boats. A Milwaukee architectural firm was hired to construct a 600-foot concrete pier. Plans were made for well-known Sarasota and Chicago architect Thomas Reed Martin to build a $30,000 magnificent Residence as a model home with the idea that the other Estate sized lots would be built with Spanish style Homes. The Mediterranean Revival style model home at 1903 Lincoln Drive was constructed in 1926. It was added to the National Register of Historic Places in 1992. There is another home on Lincoln Drive in the National Register, as well as two homes on the Sarasota County Register, one on Alta Vista Street and one on Brewer Place. The Avondale lion urns were placed on entry corners into Avondale. Two original pedestals with seating remain in place at Yale Avenue and Bahia Vista Street. At the corner of Lincoln Drive and Brewer Place, close to the ground, is the only remaining concrete street identification. At the time 41 was a humble dirt road. Deed transfers identified Avondale as a “model suburban development” and restrictions required that no dwellings be built under $5,000. Such restrictions remained in force until January 1950. Several model homes were built to attract buyers. The sales of lots increased, in part due to the frenzy and whirlwind of the Florida Land Boom. Tremendous land sales occurred in Sarasota in 1925 and Avondale quickly gained recognition as one of the finest subdivisions in the young city of Sarasota.

The homes in Avondale still reflect this rich history and range from 1920’s Spanish style to Ranch and the Colonial styles that were preferred after the war. The wide streets, lined with gorgeous mature oaks and sidewalks on both sides, encourage cool evening strolls and there are many places to choose from! Within walking distance of Downtown Sarasota, Sarasota Memorial Hospital, Southside Village, Selby Gardens and Bay-front Park, quiet and quaint, this is an ideal setting for those craving charm and the ease of location.

West of Trail Hidden Gems

The Field Club


Pacific Rim

Red Rock Park



Crazy Stuff: Little Known Facts About West of Trail

Phillippi Estate Park and Edson Keith Mansion are located on the shores of Phillippi Creek. The park includes Indian middens dating back 2,000 years proving human inhabitants and activities during prehistoric times.
Edsom Keith Mansion is listed in the National Register of Historic Places.
The second owner of the estate Mae Hansen Prodie owned the Mae Marie Company which created the concept of a wardrobe for Barbie Dolls.
Towles Court is an artist community near downtown Sarasota where you can find galleries, artist studios and Old Florida Style Homes.